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Advice for Milan - best place to pick up rental car?

We will be driving from Milan to Castellina (Tuscany), we're keeping the car for 5 days and then dropping it off in Florence (maybe the airport?). I'm trying to figure out what location to rent from in Milan. We will be staying at Hotel Berna and it looks like there is a Hertz location very near the hotel at Via Cappellini 10 but I'm worried that driving out of the city from there will be difficult.

Would picking it up from one of the airports be better? Any help is appreciated!

My husband always picked up our rental cars at the Centrale train station and returned them there also. Having said that he was very comfortable about driving in the large Italian cities, many people are not. The only time it was a sort of a nightmare was one time around 4:30PM, commute time of course but all that meant was that it took a lot longer to get out of Milan, we were on our way to Verona. Having said that he enjoyed while stalled in traffic viewing the beautiful Italian female office workers that were on their way home, lol.

Thanks everyone for the advice. I think we'll brave the drive through Milan and rent from Hertz at the Centrale train station. My husband doesn't mind driving through the city - I'm the one that gets stressed about it. We were in Athens a few years ago and mistakenly followed our GPS right through the center during the commute hour and managed to survive. I did check the route on the map and it doesn't look too bad - that is ......as long as we don't make any wrong turns!